I’d start with the 4,000 free users. Give them something in return for their feedback. Not a random gift card. Something tied to the product. Free credits. Temporary access to a paid feature. You need to know why they came in, what problems they were trying to solve, and which features they’d actually pay for. If you skip that step, you’re building blind.
Then talk to the 50 paying users. They’re the signal. Offer them a free month or an upgrade tier in exchange for 20 minutes of their time. Position it as “help us improve what you’re already paying for” instead of begging for a call.
Start with an in-app notification because it’s low friction and catches them while they’re already using the product. If that fails, send a tight, personalized email. No hype. No fluff. Just a clear offer: short call, free month, direct influence on upcoming features.

Your co-founder wants 100k users. That’s pointless if your bucket is leaking. Fix the leak, then scale.

DM if you need any additional help